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CAS 253128-41-5

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Also known as: 253128-41-5, Eribuline, Eribulina, Chebi:63587, Er 086526, E-7389 free base

Molecular Formula

C₄₀H₅₉NO₁₁

Molecular Weight

729.9 g/mol

InChI Key

UFNVPOGXISZXJD-JBQZKEIOSA-N

FDA UNII

LR24G6354G

a halichondrin B derivative that suppresses microtubule growth and acts as an antimitotic agent; structure in first source

Eribulin is a Microtubule Inhibitor. The physiologic effect of eribulin is by means of Microtubule Inhibition.

1 2D Structure

CAS 253128-41-5

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1S,3S,6S,9S,12S,14R,16R,18S,20R,21R,22S,26R,29S,31R,32S,33R,35R,36S)-20-[(2S)-3-amino-2-hydroxypropyl]-21-methoxy-14-methyl-8,15-dimethylidene-2,19,30,34,37,39,40,41-octaoxanonacyclo[24.9.2.13,32.13,33.16,9.112,16.018,22.029,36.031,35]hentetracontan-24-one

2.1.2 InChI

InChI=1S/C40H59NO11/c1-19-11-24-5-7-28-20(2)12-26(45-28)9-10-40-17-33-36(51-40)37-38(50-33)39(52-40)35-29(49-37)8-6-25(47-35)13-22(42)14-27-31(16-30(46-24)21(19)3)48-32(34(27)44-4)15-23(43)18-41/h19,23-39,43H,2-3,5-18,41H2,1,4H3/t19-,23+,24+,25-,26+,27+,28+,29+,30-,31+,32-,33-,34-,35+,36+,37+,38-,39+,40+/m1/s1

2.1.3 InChI Key

UFNVPOGXISZXJD-JBQZKEIOSA-N

2.2 Other Identifiers

2.2.1 UNII

LR24G6354G

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-(3-amino-2-hydroxypropyl)hexacosahydro-3-methoxy-26-methyl-20,27-bis(methylene)11,15-18,21-24,28-triepoxy-7,9-ethano-12,15-methano-9h,15h-furo(3,2-i)furo(2',3'-5,6)pyrano(4,3-b)(1,4)dioxacyclopentacosin-5-(4h)-one

2.3.2 Depositor-Supplied Synonyms

1. 253128-41-5

2. Eribuline

3. Eribulina

4. Chebi:63587

5. Er 086526

6. E-7389 Free Base

7. Lr24g6354g

8. 2-(3-amino-2-hydroxypropyl)hexacosahydro-3-methoxy-26-methyl-20,27-bis(methylene)11,15-18,21-24,28-triepoxy-7,9-ethano-12,15-methano-9h,15h-furo(3,2-i)furo(2',3'-5,6)pyrano(4,3-b)(1,4)dioxacyclopentacosin-5-(4h)-one

9. Dtxsid101009321

10. Nsc-707389

11. B-1939

12. Eribulinum

13. L01xx41

14. Dtxcid701436148

15. Er-86526

16. Er086526

17. Eribulin [inn]

18. (1s,3s,6s,9s,12s,14r,16r,18s,20r,21r,22s,26r,29s,31r,32s,33r,35r,36s)-20-[(2s)-3-amino-2-hydroxypropyl]-21-methoxy-14-methyl-8,15-dimethylidene-2,19,30,34,37,39,40,41-octaoxanonacyclo[24.9.2.13,32.13,33.16,9.112,16.018,22.029,36.031,35]hentetracontan-24-one

19. Er-086526

20. (2r,3r,3as,7r,8as,9s,10ar,11s,12r,13ar,13bs,15s,18s,21s,24s,26r,28r,29as)-2-[(2s)-3-amino-2-hydroxypropyl]hexacosahydro-3-methoxy-26-methyl-20,27-bis(methylene)-11,15:18,21:24,28-triepoxy-7,9-ethano-12,15-methano-9h,15h-furo[3,2-i]furo[2',3':5,6]pyrano[4,3-b][1,4]dioxacyclopentacosin-5(4h)-one

21. (1s,3s,6s,9s,12s,14r,16r,18s,20r,21r,22s,26r,29s,31r,32s,35r,36s)-20-[(2s)-3-amino-2-hydroxypropyl]-21-methoxy-14-methyl-8,15-bis(methylene)-2,19,30,34,37,39,40,41-octaoxanonacyclo[24.9.2.1(3,32).1(3,33).1(6,9).1(12,16).0(18,22).0(29,36).0(31,35)]hentetracontan-24-one

22. Eribulin Free

23. Unii-lr24g6354g

24. (1s,3s,6s,9s,12s,14r,16r,18s,20r,21r,22s,26r,29s,31r,32s,33r,35r,36s)-20-[(2s)-3-amino-2-hydroxypropyl]-21-methoxy-14-methyl-8,15-dimethylidene-2,19,30,34,37,39,40,41-octaoxanonacyclo[24.9.2.1~3,32~.1~3,33~.1~6,9~.1~12,16~.0~18,22~.0~29,36~.0~31,35~]hentetracontan-24-one (non-preferred Name)

25. Eribulin [mi]

26. Eribulin [vandf]

27. Eribulin [mart.]

28. Eribulin [who-dd]

29. B 1939

30. E7389-lf

31. Gtpl6813

32. Orb1707961

33. Chembl1683590

34. Schembl15783821

35. Ex-a4873d

36. Ufnvpogxiszxjd-jbqzkeiosa-n

37. Glxc-10730

38. Akos040740784

39. At36513

40. Db08871

41. Ncgc00510497-02

42. Bp-29357

43. Da-52974

44. Hy-13442

45. Ms-31267

46. Q408717

47. 2-[4-[[(2r)-2-aminobutyl]amino]-2-quinazolinyl]-4-chloro-phenol

48. 11,15:18,21:24,28-triepoxy-7,9-ethano-12,15-methano-9h,15h-furo[3,2-i]furo[2',3':5,6]pyrano[4,3-b][1,4]dioxacyclopentacosin-5(4h)-one, 2-[(2s)-3-amino-2-hydroxypropyl]hexacosahydro-3-methoxy-26-methyl-20,27-bis(methylene)-, (2r,3r,3as,7r,8as,9s,10ar,11s,12r,13ar,13bs,15s,18s,21s,24s,26r,28r,29as)-

2.4 Create Date

2006-10-26

3 Chemical and Physical Properties

Molecular Formula	C₄₀H₅₉NO₁₁
Molecular Weight	729.9 g/mol
XLogP3	1.1
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	12
Rotatable Bond Count	4
Exact Mass	Da
Monoisotopic Mass	Da
Topological Polar Surface Area	146
Heavy Atom Count	52
Formal Charge	0
Complexity	1380
Isotope Atom Count	0
Defined Atom Stereocenter Count	19
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

For the treatment of patients with metastatic breast cancer who have previously received at least two chemotherapeutic regimens for the treatment of metastatic cancer.

FDA Label

Halaven monotherapy is indicated for the treatment of patients with locally advanced or metastatic breast cancer who have progressed after at least one chemotherapeutic regimens for advanced disease (see section 5. 1). Prior therapy should have included an anthracycline and a taxane unless patients were not suitable for these treatments. Halaven is indicated for the treatment of adult patients with unresectable liposarcoma who have received prior anthracycline containing therapy (unless unsuitable) for advanced or metastatic disease (see section 5. 1).

Treatment of soft tissue sarcoma

5 Pharmacology and Biochemistry

5.1 FDA Pharmacological Classification

5.1.1 Active Moiety

ERIBULIN

5.1.2 FDA UNII

LR24G6354G

5.1.3 Pharmacological Classes

Established Pharmacologic Class [EPC] - Microtubule Inhibitor

5.2 ATC Code

L01XX41

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (2021) DOI:10.1021/acsenvironau.1c00008. List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

L - Antineoplastic and immunomodulating agents

L01 - Antineoplastic agents

L01X - Other antineoplastic agents

L01XX - Other antineoplastic agents

L01XX41 - Eribulin

5.3 Absorption, Distribution and Excretion

Route of Elimination

Eribulin is eliminated primarily in feces unchanged.

Volume of Distribution

43 L/m2 to 114 L/m2

Clearance

1.16 L/hr/m2 to 2.42 L/hr/m2 (dose range of 0.25 mg/m2 to 4.0 mg/m2). [FDA]

5.4 Metabolism/Metabolites

There are no major human metabolites of eribulin, CYP3A4 negligibly metabolizes eribulin in vitro.

5.5 Biological Half-Life

about 40 hours

5.6 Mechanism of Action

Eribulin inhibits the growth phase of microtubules without affecting the shortening phase and sequesters tubulin into nonproductive aggregates. Eribulin exerts its effects via a tubulin-based antimitotic mechanism leading to G2/M cell-cycle block, disruption of mitotic spindles, and, ultimately, apoptotic cell death after prolonged mitotic blockage. [FDA]

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